Hydrazine hydrate (1:1) → HCID 11130710, compound

HRID 1383454Notes

Reaction equation

HRID 1383454 reaction equation
[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][NH2:23])[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13912336HCID 13912336, compound

Product 1

HCID 11130710HCID 11130710, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[2-(4-benzhydryloxy-piperidin-1-yl)-ethyl]-isoindole-1,3-dione (0.548 g, 1.24 mmol) was dissolved in ethanol (2 ml), followed by the addition of hydrazine hydrate (large excess, 2-3 ml). The solution was refluxed for 2 hours. The white solid was precipitated. After cooling to the room temperature, the white solid was filtered off and washed with small amount of ethanol. The filtrates were combined and concentrated. The resulted residue was dissolved in toluene (100 ml). The solution was washed with water (3×20 ml) and dried over anhydrous Na2SO4. After evaporated the solvent, the crude product, 2-(4-benzhydryloxy-piperidin-1-yl)-ethylamine was obtained (0.326 g, 84.4% yield). 1H-NMR (CD3OD, ppm): 7.15-7.40 (m, 10H), 5.58 (s, 1H), 3.46 (m, 1H), 2.77 (m, 2H), 2.72 (t, 2H), 2.40 (t, 2H), 2.18 (m, 2H), 1.89 (m, 2H), 1.70 (m, 2H). ESMS 311.2 (M+1), 333.2 (M+23).

Workup

  1. temperatureThe solution was refluxed for 2 hours
  2. customThe white solid was precipitated
  3. filtrationthe white solid was filtered off
  4. washwashed with small amount of ethanol
  5. concentrationconcentrated
  6. dissolutionThe resulted residue was dissolved in toluene (100 ml)
  7. washThe solution was washed with water (3×20 ml)
  8. dry with materialdried over anhydrous Na2SO4
  9. customAfter evaporated the solvent

Sources & evidence

ORD record
ord-96539ad63287428a9363fc67bd280be1
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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